Caravaggio's Rome: Masterpieces, Brawls and a Killing

Follow Caravaggio through Rome, from the Cerasi Chapel to the Contarelli Chapel, past his landlady's alley, the street of the 1606 killing and the prison he knew too well

Rome · 11 stops · 26 min audio · Generated October 2026

1. Santa Maria del Popolo: The Cerasi Chapel

Piazza del Popolo 12, 00187 Roma RM, Italy

Step inside the church, walk up the nave toward the high altar, and turn into the small chapel just to its left. Two paintings face each other across a space so narrow that you can hardly step back from them... and that is exactly how Caravaggio meant you to meet them: up close, from the side, almost inside the scene.

In 1600 Tiberio Cerasi, treasurer-general to the pope, bought this chapel and hired the two most talked-about painters in Rome. Annibale Carracci painted the Assumption over the altar; Caravaggio got the side walls, the Conversion of Saint Paul and the Crucifixion of Saint Peter. His first versions were set aside, and he painted these two in their place. One of the rejected ones, a very different Conversion, still survives in a private collection in Rome.

Look at Saint Paul: thrown flat on his back, arms open, eyes shut, blinded by a light we cannot see, while an enormous piebald horse fills almost the whole picture, one hoof carefully lifted so as not to trample him. No heavenly host, no Christ in the clouds. A story goes that someone asked the painter why he had put a horse in the middle instead of God. Because, he supposedly answered, the horse is standing in God's light.

Opposite, Saint Peter is being hauled upside down on his cross by three labourers. You hardly see their faces. You see their effort: a back straining under the beam, a man hauling on a rope, the dirty soles of feet turned toward you. Peter, old and heavy, lifts his head and looks not at heaven but past us. It is a painting about work, weight and fear, hung in a rich man's chapel.

When Caravaggio arrived in Rome in the early 1590s, a penniless young painter from Lombardy, he very likely walked in through the city gate right beside this church, the main road from the north. Within ten years he was painting for the pope's treasurer. Within fifteen he would be a fugitive with a price on his head. Walk out, cross the square, and take Via del Babuino, the street on the left of the twin churches, looking for a stone figure everybody used to insult.
2. The Babuino: A Talking Statue and a Libel Trial

Via del Babuino, 00187 Roma RM, Italy

Partway down the street, beside the church of Sant'Atanasio dei Greci, a battered stone figure lounges above a fountain basin, so worn and so ugly that Romans named him the baboon, il babuino. The street took its name from him. He is really an ancient Silenus, a drunken companion of Bacchus, and he is one of Rome's talking statues.

In papal Rome, where you could not criticise a pope or a cardinal openly, people hung anonymous verses on a handful of old statues at night. Pasquino, near Piazza Navona, was the most famous, but the Babuino joined in, and so did a few others. The verses were sharp, funny and often obscene, and by morning half the city had read them.

Caravaggio lived inside this culture of anonymous verse, and in 1603 it landed him in court. A rival painter, Giovanni Baglione, sued him, his friend Orazio Gentileschi and the architect Onorio Longhi for spreading poems that mocked Baglione and his new Resurrection for the Jesuit church. The verses were crude, full of jokes about his talent and worse. Caravaggio denied having written them.

The court record is one of the few places where we hear Caravaggio's own voice. Asked which painters he thought good, he named a few, and explained that a good painter, a valentuomo, is one who knows how to paint well and how to imitate natural things well. In one sentence, he summed up his whole revolution: paint what you actually see. He spent about two weeks in prison, and was let out thanks to the intervention of the French ambassador.

Baglione got the last word, though. Decades later he published a book of artists' lives, including Caravaggio's, full of grudging praise and poisoned little details, and much of what we think we know about the painter still comes from his enemy. Keep walking toward Via del Corso, and turn south along it to a huge domed church built by the Lombards of Rome.
3. San Carlo al Corso: The Church of Caravaggio's Brawling Friend

Via del Corso 437, 00186 Roma RM, Italy

On Via del Corso, look up at the huge, rather severe front and the great dome of the church of Santi Ambrogio e Carlo, which every Roman simply calls San Carlo al Corso. It belongs to the Lombards, the community of people from Milan and its region living in Rome. And Caravaggio, never forget, was a Lombard.

Michelangelo Merisi was born in 1571, most likely in Milan, to a family from the small town of Caravaggio, which gave him the name the world remembers. In Rome he spoke with a northern accent, drank with northerners, and leaned on a network of Lombard friends. One of the most loyal, and the most hot-headed, was the architect Onorio Longhi, son of a well-known builder, a man with a quick tongue and a quicker sword.

Longhi was a co-defendant in the libel case you just heard about, and he stood beside Caravaggio in more than one street quarrel. On the evening of 28 May 1606, when Caravaggio killed Ranuccio Tomassoni, Longhi was there too, and he also had to flee Rome. The two of them were like a pair of loaded pistols walking down the same street.

And here is the twist. This church is Longhi's. Once he was back in Rome and back in favour, the Lombard confraternity hired him, and work on the new church began in 1612 to his designs, continued after his death by his son, Martino Longhi the Younger. The dome came decades later, designed by Pietro da Cortona. So the brawler who stood next to Caravaggio in a fatal fight ended up building one of the biggest churches on Rome's main street.

The church is dedicated to Saint Charles Borromeo, the reforming archbishop of Milan, and keeps his heart as a relic. Caravaggio grew up in Borromeo's Milan, a city of plague, penance and fierce, plain-spoken piety, and many scholars see that severe Lombard faith in his saints with their bare, dirty feet. Now cross into Largo Goldoni and follow Via della Fontanella di Borghese west, to a palace shaped like a harpsichord.
4. Palazzo Borghese: The Cardinal Who Held the Pardon

Largo della Fontanella di Borghese, 00186 Roma RM, Italy

Stand in the little square and take in the long front of the palace with its rows of tall windows. Seen from above, this building has the shape of a harpsichord, which is why Romans nicknamed it il cembalo, and in Caravaggio's last years it was the home of one of the most insatiable art collectors Europe has ever known.

In 1605 Camillo Borghese became Pope Paul the Fifth and, as popes did, made his nephew Scipione a cardinal and showered him with money and power. Scipione wanted beautiful things, and he wanted them badly. In 1607 the painter Cavalier d'Arpino, in whose workshop the young Caravaggio had once painted fruit and flowers, ran into legal trouble. His collection was confiscated and ended up with Scipione, including two early Caravaggios, the Boy with a Basket of Fruit and the Sick Bacchus.

By then Caravaggio was gone. After the killing of 1606 he was under a capital sentence, the bando capitale, which meant that anyone could kill him without being punished. His only hope was a papal pardon, and the road to the pope ran through this palace, through the nephew who loved his paintings.

So he painted his way toward forgiveness. In David with the Head of Goliath, now in the Galleria Borghese, the severed head dangling from David's hand has Caravaggio's own face, exhausted, mouth hanging open. It is often read as a plea: here is my head, do with it what you will. In 1610, hearing that a pardon was close, he sailed north from Naples with paintings meant for Scipione... and died at Porto Ercole, on the Tuscan coast, probably of a fever, before he ever saw Rome again. He was thirty-eight.

Scipione got his pictures anyway. The Borghese collection later moved to the family villa in the great park, the Galleria Borghese, where six Caravaggios still hang together. From here, head south into the tangle of lanes, toward the quiet Vicolo del Divino Amore, where Caravaggio once rented a house... and fought with his landlady.
5. Vicolo del Divino Amore: The Painter and His Landlady

Vicolo del Divino Amore, 00186 Roma RM, Italy

Walk into this quiet, slightly crooked alley and picture it around 1605: washing hung between the windows, mud underfoot, a few rented rooms, and somewhere along here, a painter's door. This is where Caravaggio rented a small house, with one room big enough to work in.

We know a surprising amount about that house because of an inventory drawn up in August 1605, when his landlady, Prudenzia Bruni, had his belongings seized for unpaid rent. The list is touchingly small: a few chairs and stools, a table, a guitar and a violin, swords and daggers, a handful of books, a large mirror, and a pile of canvases, some still blank. The most famous painter in Rome owned almost nothing.

Her loudest complaint was the ceiling. Caravaggio had cut a hole in it. Nobody knows exactly why: to fit a canvas too tall for the room, perhaps, or to let a shaft of light fall from above. Either way, it is hard not to think of his paintings, where a single hard beam cuts across a dark room and picks out a face, a hand, a shoulder.

Things went downhill fast. Locked out, Caravaggio came back at night and threw stones at her windows, and she filed a complaint against him. That same summer he wounded a notary, Mariano Pasqualone, in a quarrel over a woman named Lena, one of his models, and had to slip away to Genoa for a few weeks until the matter was patched up. His friends and patrons were spending more and more of their time getting him out of trouble.

Lena, it is believed, posed for one of his most beautiful Madonnas, and you are going to meet her face in a church in a few minutes. But first, a few steps south, there is a short street with a sporting name, where the worst evening of his life began. Follow the lane to Via di Pallacorda.
6. Via di Pallacorda: The Killing of Ranuccio Tomassoni

Via di Pallacorda, 00186 Roma RM, Italy

Stop in this short street and read its name on the marble plaque at the corner: Via di Pallacorda. Pallacorda was an early form of tennis, played with a ball hit over a cord stretched across a court, and around 1600 there was a court for it in this neighbourhood. On the evening of Sunday, 28 May 1606, the most famous painter in Rome killed a man near here.

The victim was Ranuccio Tomassoni, from a family of soldiers from Terni with powerful protectors and a firm grip on this district. The two men had history. Gossip at the time spoke of a bet on a tennis match; others talked of a debt, or of a woman, perhaps the courtesan Fillide Melandroni, who had posed for Caravaggio. Many historians now think it was a planned fight between two small armed groups, settled with swords.

Swords came out. Caravaggio was wounded in the head. Tomassoni went down with a deep wound high in the thigh and bled to death. One modern biographer has suggested that Caravaggio was trying to mutilate him, the kind of humiliation reserved for a rival in love... but that is a reading, not a fact, and the truth of that evening is lost.

Caravaggio fled the same night, first to the estates of the Colonna family in the hills south of Rome, then to Naples. He never saw this city again. Condemned to death in his absence, he spent his last four years running: Naples, Malta, Sicily, Naples again. In Malta he was made a knight, then thrown into prison and expelled. In Naples he was ambushed and his face was badly slashed.

And yet those are the years of his darkest and greatest paintings, huge canvases full of silence and shadow. It is hard to reconcile the man with the sword in this street with the tenderness of what you are about to see. Cross Via della Scrofa and walk south-west to the broad steps of the church of Sant'Agostino.
7. Sant'Agostino: The Madonna with the Dirty Feet

Piazza di Sant'Agostino 80, 00186 Roma RM, Italy

Climb the wide steps, push open the door and turn to the first chapel on your left. Above the altar, a young mother with a big, heavy child in her arms leans in a doorway, and two kneeling pilgrims gaze up at her. Before anything else, look down... at the man's feet.

This is the Madonna di Loreto, also called the Madonna of the Pilgrims, painted around 1604 to 1606 for the Cavalletti family chapel. At Loreto, on the Adriatic coast, pilgrims venerated the Holy House of Nazareth, believed to have been carried there by angels. Caravaggio turns the miracle into a scene on a Roman doorstep. The Virgin's doorway is a crumbling wall with peeling plaster, and she has no throne, no clouds, no angels, only one bare foot crossed over the other.

And then the pilgrims: an old woman in a dirty bonnet, and a man whose bare feet, black soles and all, are thrust straight out at the viewer, at about the height of your face if you kneel at the altar rail. His rival Baglione wrote that the common people made an enormous fuss about it. Some loved it, because here at last were people like them. Others thought it an insult to the Mother of God.

The model for the Virgin is generally believed to be Lena, Maddalena Antognetti, the woman over whom he attacked the notary. A woman from the streets around Piazza Navona, posing as the Madonna, over the altar of a church in the heart of papal Rome. Everybody in the neighbourhood would have recognised her.

Before you leave, look for Raphael's fresco of the prophet Isaiah on a pillar of the nave, and Jacopo Sansovino's marble Madonna del Parto near the entrance, her foot worn smooth by generations of hopeful mothers-to-be. Three very different ideas of holiness under one roof. Then walk west, toward the river, to Via di Tor di Nona and the site of a prison Caravaggio knew far too well.
8. Tor di Nona: The Prison by the River

Via di Tor di Nona, 00186 Roma RM, Italy

Walk along Via di Tor di Nona, a narrow riverside street with old houses on one side and the high embankment of the Tiber just beyond. You won't find a tower here any more, but for centuries a medieval tower stood near this spot... and the popes used it as a prison.

Caravaggio knew the inside of Tor di Nona well. The police archives of Rome are full of him: arrested for carrying a sword and dagger without the right papers, for insulting officers, for throwing stones at the guards. After the libel trial of 1603 he spent his two weeks behind bars in this prison, until the French ambassador spoke up for him.

His most famous offence was culinary. In April 1604, in a tavern called the Osteria del Moro, he asked a waiter which of the artichokes on his plate had been cooked in butter and which in oil. The waiter told him to smell them and find out. Caravaggio threw the plate, artichokes and all, in the man's face, and, according to the waiter's complaint, reached for his sword.

Justice was never far away in this corner of the city. A few hundred metres upriver, in the square at the head of the bridge to Castel Sant'Angelo, Rome held its public executions. In September 1599 the young noblewoman Beatrice Cenci was beheaded there before an enormous crowd, for the murder of her violent father. It is often said that Caravaggio was among the spectators, and some see that day in his Judith Beheading Holofernes.

The prison's afterlife is pure Rome. In 1671 a theatre, the Tordinona, opened on the site, with the support of Queen Christina of Sweden, and became the first public opera house in the city. Prisoners out, sopranos in. Now turn your back on the river and walk south-east into the lanes, to the palace where Caravaggio's career really took off.
9. Palazzo Madama: Cardinal del Monte's House Painter

Corso del Rinascimento, 00186 Roma RM, Italy

Face the grand Baroque front of Palazzo Madama, with its carabinieri at the door and the flags above. Since 1871 it has been the seat of the Italian Senate. Around 1595 it was the home of a cardinal who changed Caravaggio's life.

The palace belonged to the Medici, the grand dukes of Tuscany, and its name remembers Madama Margaret of Austria, daughter of the emperor Charles the Fifth, who once lived here. In Caravaggio's time it housed Cardinal Francesco Maria del Monte, the Medici's man in Rome: diplomat, music lover, amateur alchemist, and a collector with a very sharp eye. Del Monte bought a painting called The Cardsharps from a dealer near here, and soon took the young man who had painted it into his household, with a room, meals and an allowance.

For about five years Caravaggio lived here and painted for the cardinal's sophisticated circle. The Cardsharps, with its innocent boy and the older cheat signalling over his shoulder through a glove with the fingertips worn through. The Musicians, a tangle of soft-faced young men tuning a lute over their sheets of music. And, as a diplomatic gift for the grand duke in Florence, a shield painted with the screaming, snake-haired head of Medusa.

Del Monte also owned a small villa on the hill near today's Via Veneto, where Caravaggio painted his only known ceiling: Jupiter, Neptune and Pluto, the gods of the elements, seen from directly below, as if you were lying on the floor. Some say all three have the painter's own face. The villa is still in private hands, and that ceiling is one of the least seen masterpieces in Rome.

The cardinal was also one of the men who ran the finances of Saint Peter's, and his influence is thought to have helped his protégé win his first great public commission, in a church around the corner, for the French community of Rome. Walk along the palace to its northern end and turn right: the church door is only a few steps away.
10. San Luigi dei Francesi: The Contarelli Chapel

Piazza di San Luigi de' Francesi, 00186 Roma RM, Italy

Walk down the left aisle of the church of the French nation to the last chapel before the altar, and give your eyes a moment. Three enormous canvases wrap around you, and in the one on the left, a beam of light cuts across a dark room toward a group of men counting money at a table.

The chapel was paid for by a French cardinal, Matthieu Cointrel, Contarelli in Italian, who died in 1585 and left money for scenes from the life of his namesake, Saint Matthew. The project stalled for years. In 1599 it went to Caravaggio, his first public commission, and in 1600 the Calling and the Martyrdom of Saint Matthew were unveiled. Almost overnight he became the most discussed painter in Rome.

In the Calling, Christ enters from the right, half hidden behind Saint Peter, and points with a languid hand that echoes Michelangelo's Adam on the Sistine ceiling. The light in the painting falls from the same direction as the real window above the altar, so the scene seems lit by the church itself. At the table, dressed in the latest fashions of 1600, the tax collectors look up. Which one is Matthew? The bearded man pointing at himself, as if to say, who, me?... or the young man slumped at the end, still counting coins? Scholars argue about it to this day.

Even here he had trouble. His first altarpiece for the centre, Saint Matthew and the Angel, showed the saint as a bald, bare-legged peasant, with an angel guiding his hand like a schoolboy's. The clergy refused it, and Caravaggio painted the more dignified version you see now. The rejected one ended up in a Berlin museum... and was destroyed at the end of the Second World War, in 1945.

Now look into the Martyrdom on the right. Behind the killer, a bearded man with a pained face peers out of the crowd: it is generally recognised as a self-portrait of Caravaggio, aged about twenty-nine, watching a murder. Six years later he would commit one. For the last stop, walk east past the Pantheon and on to Via del Corso, to a family palace that still keeps two of his earliest masterpieces.
11. Galleria Doria Pamphilj: Sleep and Sorrow

Via del Corso 305, 00186 Roma RM, Italy

Here on Via del Corso, the long, grand front of Palazzo Doria Pamphilj hides one of the great private art collections of Rome, still owned by the family whose name it carries. Inside, in rooms of gilded frames and mirrors, hang two of Caravaggio's most tender early paintings.

The first is the Rest on the Flight into Egypt, painted in the second half of the 1590s. The Virgin has fallen asleep with the baby in her arms, her head bent over his. Joseph, an old man with tired, bare feet, holds up a sheet of music for an angel who plays the violin, seen from behind, his white wings filling the centre of the picture. The music is real: scholars have identified it as a motet by the Flemish composer Noël Bauldeweyn, set to words from the Song of Songs.

The second, the Penitent Magdalene, shows a young red-haired woman sitting on a low chair, head bowed, her jewels and a broken string of pearls scattered on the floor beside her. A single tear runs down her cheek. And notice: she is the same model as the sleeping Virgin next door, a young courtesan often identified as Anna Bianchini, whose name turns up in the police records of the time.

That was Caravaggio's quiet scandal, and his genius. He put real Romans, people you could pass in the street outside, into the holiest roles, and painted them with such care that their dignity was impossible to deny. Nicolas Poussin is said to have remarked that he came into the world to destroy painting. Within a generation, painters from Utrecht to Seville were copying him.

So the walk ends with its beginning. You followed him from the gate where he arrived, through the cardinal's palace, the churches that made him famous, the alley of his landlady, the street of the killing and the prison by the river, to these two calm pictures of sleep and sorrow, painted when he was still young and almost unknown. Caravaggio lived thirty-eight years, and the city outside these doors still carries his footsteps.